Dual Photochemical H-Atom Transfer and Cobalt Catalysis for the Desaturative Synthesis of Phenols from Cyclohexanones

Angew Chem Int Ed Engl. 2023 Jun 19;62(25):e202301656. doi: 10.1002/anie.202301656. Epub 2023 May 9.

Abstract

Phenols are integral aromatic molecules widely encountered in the structure of natural products and routinely utilised for the synthesis of high-value materials. Accessing highly substituted derivatives can often be difficult, especially when their functionalization pattern does not match the intrinsic reactivity leveraged by electrophilic aromatic substitution (SE Ar) chemistry. Here, we provide an alternative and mechanistically distinct approach for phenol synthesis using saturated cyclohexanone precursors. This process operates at ambient temperature, under simple purple light irradiation, and features a dual catalytic manifold carrying four sequential H-atom transfer processes.

Keywords: Cobalt Catalysis; Desaturation; H-Atom Transfer; Phenols.

MeSH terms

  • Catalysis
  • Cobalt
  • Cyclohexanones* / chemistry
  • Phenols* / chemistry

Substances

  • Phenols
  • Cyclohexanones
  • Cobalt